O-Toluidine → HCID 86745484, compound

HRID 1534472Notes

Reaction equation

HRID 1534472 reaction equation
C([C:6]1[C:7](=O)[NH:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][C:12]([CH2:17][O:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:11][CH:10]=2)(=O)CCC.NC1C(C)=CC=CC=1>O1CCOCC1>[C:19]([O:18][CH2:17][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:15]2)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 7242O-ToluidineHCID 19909675HCID 19909675, compound

Product 1

HCID 86745484HCID 86745484, compoundYield 108.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-butyryl-4-chloro-6-benzoyloxymethylquinolone (10 g, 30 mmol) and o-toluidine (3.7 ml, 35 mmol) were heated together under reflux in 1,4-dioxan (150 ml) for 1.5 hours. The solvent was evaporated and the residue dissolved in chloroform, washed with 2 M HCl, sodium hydrogen carbonate solution (x2) and brine, dried, filtered and evaporated to an oil which immediately crystallized to give 3-butyryl-4-2-methylphenylamino)-6-benzoyloxymethyl quinoline (8.6 g, 66%), m.p. 142° C.-4° C.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in chloroform
  3. washwashed with 2 M HCl, sodium hydrogen carbonate solution (x2) and brine
  4. customdried
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customimmediately crystallized

Sources & evidence

ORD record
ord-9b882b879c2f49d2a16666805194ffad
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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